Toluene → tert-butyl 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carbamate

HRID 1296469Notes

Reaction equation

[CH3:1][N:2]1[C:6]([C:7]2[S:11][C:10](C(O)=O)=[CH:9][CH:8]=2)=[CH:5][C:4]([C:15]([F:18])([F:17])[F:16])=[N:3]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C([N:38]([CH2:41]C)CC)C.C1(C)C=CC=CC=1.[C:50]([OH:54])([CH3:53])([CH3:52])[CH3:51]>>[CH3:1][N:2]1[C:6]([C:7]2[S:11][C:10]([NH:38][C:41]([O:54][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:26])=[CH:9][CH:8]=2)=[CH:5][C:4]([C:15]([F:16])([F:17])[F:18])=[N:3]1

Participants

Reactant 5

HCID 1140Toluene

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 27756685-(1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-2-thiophenecarboxylic acid

Product 1

HCID 22288380tert-butyl 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carbamate

Conditions

Temperature: 50 °C

Procedure

A mixture of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acid, diphenylphosphoryl azide, triethylamine and toluene was stirred at 50° C. for 30 minutes. Then, tert-butanol was added to the reaction solution. After stirring at 80° C. for 5 hours, it was subjected to purification in the usual way to give tert-butyl 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carbamate as light yellow crystals.

Workup

stirringAfter stirring at 80° C. for 5 hours
customit was subjected to purification in the usual way

Sources & evidence

ORD record: ord-d613c7fa88e64f2fb638323e869eb3c4
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07247635B2

Reaction notes

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